Potassium Carbonate → HCID 23196870, compound

HRID 1029713Notes

Reaction equation

HRID 1029713 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[CH3:5][N:6]([C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1)[N:7]1[C:15]2[C:10](=[CH:11][C:12]([OH:16])=[CH:13][CH:14]=2)[CH:9]=[CH:8]1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH3:1][NH:2][C:3](=[O:4])[O:16][C:12]1[CH:11]=[C:10]2[C:15](=[CH:14][CH:13]=1)[N:7]([N:6]([CH3:5])[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1)[CH:8]=[CH:9]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12228Methyl IsocyanateHCID 19900479HCID 19900479, compound

Product 1

HCID 23196870HCID 23196870, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl isocyanate (0.72 g) was added to a solution of 1-(methyl-4-pyridinylamino)-1H-indol-5-ol (2.5 g) in 75 mL tetrahydrofuran containing milled potassium carbonate (2 g). After stirring three hours at ambient temperature the mixture was filtered and concentrated. The residue was eluted through silica with ethyl acetate via flash column chromatography to yield a solid 3.1 g. This was eluted through silica with 5% methanol in dichloromethane via HPLC to yield 2.6 g solid, m.p. 186°-188° C. This was recrystallized from 20% methanol in ether to yield 1.6 g of product, m.p. 186°-188° C.

Workup

  1. filtrationwas filtered
  2. concentrationconcentrated
  3. washThe residue was eluted through silica with ethyl acetate via flash column chromatography

Sources & evidence

ORD record
ord-f6579f156ef042d3a1a3fcf3ca813679
Source dataset
uspto-grants-1992_04
Patent number
US05102891

Reaction notes

Loading…